Patent GB-642013-A (GB)
Title: Process for the manufacture of a new acylated sulphonamide, and of its salts
IPC: C07C311/45
Filed: 1948-04-02
Abstract: An acylated sulphonamide of the formula <FORM:0642013/IV (b)/1> is prepared by (a) acylating a sulphonamide of the formula <FORM:0642013/IV (b)/2> with p-isopropoxybenzoic acid or with a reactive derivative thereof, and converting the group R1 to an amino group, (2) condensing a benzene-sulphonyl halide of formula R1-C6H4-SO2-Hal with a metal compound of p-isopropoxybenzamide, and converting the group R1 to an amino group, or (3) condensing a reactive derivative of benzenesulphonic acid of the formula R1-C6H4-SO3H with a p-isopropoxy benziminoether or a p-isopropoxybenzamidine of the general formula <FORM:0642013/IV (b)/3> to give a product of formula <FORM:0642013/IV (b)/4> and then hydrolysing the group -N = CR2-to a -NH-CO- group and converting the group R1 to an amino group.  In the above formul  R1 is a nitrogen-containing group convertible to an amino group, e.g. an acylamino, nitro, p-benzeneazo or p-benzeneazoxy group, and R2 is an alkoxy, aryloxy or amino group.  Salts of the new sulphonamide may be prepared, e.g. with inorganic or organic bases, several of which are specified.  The p-amino groups in the sulphonamide may be acylated with high molecular fatty acids to produce capillary active products. In examples: (1) p-isopropoxy-benzoyl chloride and p-nitrobenzenesulphonamide are refluxed in the presence of chlorobenzene and copper powder (or ferric chloride or aluminium chloride) and the product reduced with iron filings and acetic acid; alternatively the intermediate product may be obtained by condensing p-isopropoxybenzoic acid with p-nitrobenzenesulphonamide in the presence of phosphorus pentachloride or pentoxide; (2) p-isopropoxybenzoyl chloride is refluxed with p-carbomethoxyamino - benzene - sulphonamide, chlorobenzene and copper powder and the product saponified to give N1-(4-isopropoxybenzoyl)-p-aminobenzenesulphonamide which is then converted to its calcium salt; (3) p-isopropoxybenzoyl chloride, p-acetylaminobenzenesulphonamide, nitrobenzene and copper powder are heated together and the product hydrolysed; (4) p-isopropoxybenzoyl chloride is added to p-nitrobenzenesulphonamide in pyridine or other acid-binding medium, and the product reduced with iron powder, hydrochloric acid and alcohol; (5) 4-isopropoxybenzoyl chloride is added to the sodium salt of p-nitrobenzenesulphonamide in nitrobenzene and the product reduced with iron and acetic acid; (6) p-nitrobenzenesulphonyl chloride in xylene is added to p-isopropoxybenzamide which has been heated with sodium amide, and the product is reduced with nickel and hydrogen; (7) p-nitrobenzenesulphonyl chloride is added to a suspension of p-isopropoxybenzamidine hydrochloride in pyridine, the product reduced, and the N - (4 - aminobenzenesulphonyl) - 41 - isopropoxybenzamidine obtained is hydrolysed with dilute hydrochloric acid; instead of p-isopropoxybenzamidine the corresponding imino-ethyl ether may be employed; (8) the ethylenediamine salt of N1-(4-isopropoxybenzoyl)-p-aminobenzenesulphonamide is prepared by adding ethylenediamine to an absolute methyl alcoholic solution of the sulphonamide; other organic or inorganic bases, e.g. diethylamine and ethylamine, may be used similarly. Specification 560,661 is referred to.ALSO:Capillary active products suitable for use as washing, emulsifying or wetting agents are obtained by acylating with high molecular fatty acids the p-amino group in the compound N1 - (4 - isopropoxybenzoyl) - p - aminobenzenesulphonamide.